In my even more humble opinion.
Rather than making this a long-as-heck list, I'll give you my top nine picks.
Why nine? Because ten is so overdone and eleven would be too predictable.
Movies:
9. Electric Dreams - Go ahead. Ask me.
8. The Goonies - I always liked Adventure films. This one is for the kid in all of us.
7. The Godfather I & II - Two movies you can't refuse. Avoid the third one.
6. Star Wars - The original version, if you please.
5. The Shawshank Redemption - Such an important movie on many levels.
4. Dead Poet's Society - Ditto
3. Stand By Me - Not usually a fan of King's movies but this one had me from "Hello."
2. The Empire Strikes Back - So much better than all the other Star Wars movies combined.
1. Shaun of the Dead - My #2 used to be #1 until I saw this extremely well done movie.
TV Shows:
9. Friends - A guilty pleasure I'd probably never admit to. Oops. I just did.
8. "V" - Back in the day series about alien invasion. Pretty well done, too.
7. Quantum Leap - I kinda miss this show. Even though it was kinda cheesy.
6. Everwood - Classy drama that I don't get to see much. I lost track of it, though. 
5. Smallville - Ditto above. Have first two seasons on DVD.
4. Dead Like Me - Quirky drama. Loved the first season. Ain't too sure about the second.
3. The Simpsons - This one should be pretty obvious.
2. Family Ties - Another back in the day series.
1. Cowboy Bebop - The. Best. Show. Ever.
Note: I'll have no comments about how great the O.C. is, and how I must see it, in this article. Do so and I may just stick my tongue out at you.